As the Vineyard readies itself for Memorial Day weekend, the traditional start to the summer season, Island businesses say excitement outweighs uncertainty for the first time in many years, but that both emotions are still present. In interviews with over a dozen Island business owners, transportation and board of trade officials, many said all signs are pointing to a busy summer, but also stressed the fluctuating state of the pandemic, continued supply chain woes and the annual crunch for staff as reasons why they will need to be flexible throughout the season.

And a strong shoulder season has meant the busy season has already arrived for many.

Kelly Sciandra, who runs the kitchen at Nancy’s Snack Bar in Oak Bluffs, said last weekend’s opening was like none he’s seen in his 14 seasons on the Island.

“Honestly, it was the busiest opening weekend that I can remember,” he said.

Oak Bluffs Association executive director Christine Todd said excitement is already permeating the entire Oak Bluffs business community.

“Kind of feeling like the floodgates

Gearing up for a ride around the Island — Ray Ewing

have opened up,” she said. “There’s a lot of good energy going around — anticipating a great season ahead.”

Brook Katzen, owner of the Cove Golf and Grill, Mad Martha’s and Little House Cafe in Vineyard Haven, agreed.

“Across the board, we’re expecting the biggest summer ever,” he said.

But as Covid cases remain high on the Island, excitement is underscored by apprehension and mask advisories. The Vineyard has held a high Covid risk categorization for nearly two weeks, based on CDC risk assessment

metrics. Cases have dipped slightly in recent days, but remain well above the high risk threshold.

Tisbury health agent Maura Valley said the best way to prevent the spread of Covid is to wear a mask in crowded areas, socially distance and congregate outside when possible.

“What we’re recommending is the same thing we’ve been saying all along,” she said. “Cases are high.

Ms. Valley added that the rise in cases isn’t likely to subside anytime soon — especially not after a busy holiday weekend.

“I wouldn’t expect to see the numbers drop for at least another couple of weeks after this,” Ms. Valley said.

Ready rock on Circuit avenue. — Ray Ewing

Steamship Authority advance reservation numbers indicate busy weekends will be a trend throughout the summer. Spokesman Sean Driscoll said the ferry line has booked 65,286 trips to the Vineyard from June through August so far this year, a 1.3 per cent increase over the same time last year. Trips back to Woods Hole are exactly even with last year, with 62,648 advance reservations. Available spots on ferries to the Vineyard for Memorial Day weekend are few and far between, Mr. Driscoll added.

“Memorial Day is booked,” he said. “If anyone was trying to book a car right now they’d have a few options, but not many.”

But there are always bicycles to rent for those unable to get a car over, which is a boon to Phil Hughes, owner of Wheel Happy bike shop in Edgartown. Mr. Hughes said while bicycle reservations for the coming weeks have been similar to year’s past, people are renting for longer. He suspects that has something to do with the ferry because people still need a way to get around even without a car.

“Because boat reservations are harder to come by, right now I’m starting to see more and more people renting for the week because they can’t bring a car over,” Mr. Hughes said.

This week will also see an increase in flights going in and out of the Martha’s Vineyard Airport, according to airport director Geoffrey Freeman. Delta will begin flights out of LaGuardia while JetBlue will shuttle passengers between the Vineyard and Washington, Newark, New York and Boston.

“We’re anticipating a strong weekend,” Mr. Freeman said. “Looks like it’s going to be a good weekend for flying.”

Early, unofficial reports that preparations were under way at the airport for a visit from Vice President Kamala Harris to the Island over the holiday weekend had changed by Friday, when airport director Geoff Freeman confirmed that the visit had been canceled.

Flags up for the holiday weekend. — Mark Alan Lovewell

Memorial Day weekend also means the debut of new shops and cafes on main streets. In addition to his job at Nancy’s, Mr. Sciandra opened Aalia’s Coffee with his wife Joy Younan, a new cafe on Kennebec avenue in Oak Bluffs.

“Good music, good coffee and a blend of Italian and Lebanese cuisine,” Mr. Sciandra said.

In Vineyard Haven, three new clothing shops will open on Main street this summer. Lapie and Island Vintage are now part of the downtown mix, joining second-hand clothing store Act Two which opened this spring.

“I don’t think we’ll have much in the way of open store fronts,” said Sarah York, manager of CB Stark jewelry store and head of the Vineyard Haven Business Association.

And one familiar Edgartown shop will move to a new home. Nell, the women’s clothing store currently located at the foot of Main street, will relocate to the former Sundog location, which closed down in March after nearly 50 years in business on the Island.

Nell owner Mairéad MacClarence said she will now offer men’s clothes as a way to pay homage to the old haberdashery. Ms. MacClarence, a lifelong Islander who has owned the store for the last six years, noted she has big shoes to fill and feels a sense of obligation to do the storefront justice.

Sprucing up the deck at the Atlantic in Edgartown. — Ray Ewing

“It was an institution — it was such an incredible store, such a unique store. We have loved Sundog forever,” Ms. MacClarence said. “I’m taking over the space with a real understanding of how important it is to the town and to the community. I hope that I can only make people happy.”

Despite predictions for a banner summer, business owners say staffing troubles stemming from the pandemic still linger. Doug Abdelnour, owner of Nancy’s and Nomans in Oak Bluffs, said uncertainty still surrounds the H-2B and J-1 visas that contribute to much of the Island’s summer workforce. Visitors can expect longer wait times for service, they said.

“We’re kind of running with a skeleton crew, and that’s kind of the plan for the whole summer,” he said. “The menus are a little more streamlined than we’d like to see them . . . it’s like a balancing act.”

Ms. MacClarence, who traditionally hires college students, said this year her store occupies a middle ground between life before the pandemic when staffing was hard but manageable and the dire shortage of workers she experienced last summer.

“I’ve definitely seen a tick back to normal in regards to finding help,” she said. “Last year was infinitely worse than this year seems to be. But the difficulty is that as the season gets busier, the college students leave and go back to school. Come August 18, I’m going to be in a hurting place.”

A strong contingent of last year’s employees will return to Edgartown Books, manager Mat Tombers said. The bookstore will also hire two international employees who could not come to the Island last year due to the pandemic.

“I feel incredibly lucky, and let’s just hope that luck holds,” Mr. Tombers said.

Last year provided a lesson when it came to inventory, he added. The unreliable supply chain meant he was constantly worried about keeping the shelves stocked.

“This year I’m trying to anticipate a robust summer and have inventory in stock and not have to do last minute ordering,” Mr. Tombers said.

Weather also plays an integral part in the business cycle. A generally sunny Memorial Day weekend might be dampened by some rain Saturday, but a little rain here and there is good for business, Ms. MacClarence said.

“We need one rainy day every so often because otherwise people are at the beach all day. Love that, want you to go to the beach, but we also want you to be in town too,” she said.